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The 9,10-anthra­quinone ring system of the title compound, C25H26O5, is essentially planar. The O-geranyl substituent is at the meta position with respect to the hydroxyl group. O—H...O intramolecular hydrogen bonds are observed in the molecular structure. The molecules form centrosymmetric hydrogen-bonded dimers via intermolecular C—H...O hydrogen bonds which generate rings of motif R22(10). The crystal structure is further stabilized by weak π–π interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805001674/ci6514sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805001674/ci6514Isup2.hkl
Contains datablock I

CCDC reference: 264064

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.086
  • wR factor = 0.219
  • Data-to-parameter ratio = 13.4

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for O3 - C10 .. 11.19 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C21
Alert level C PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.43 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.74 Ratio PLAT230_ALERT_2_C Hirshfeld Test Diff for C21 - C22 .. 5.15 su PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C20 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C17 PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C5 -C10 1.45 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 7 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 7 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2003).

3-(3,7-Dimethylocta-2,6-dienyloxy)-1,8-dihydroxy-6-methyl-9,10-anthraquinone top
Crystal data top
C25H26O5Z = 2
Mr = 406.46F(000) = 432
Triclinic, P1Dx = 1.279 Mg m3
Hall symbol: -P 1Melting point = 391–392 K
a = 4.6082 (1) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.965 (4) ÅCell parameters from 1719 reflections
c = 18.105 (5) Åθ = 1.0–28.1°
α = 100.074 (5)°µ = 0.09 mm1
β = 92.978 (5)°T = 293 K
γ = 96.526 (5)°Needle, orange
V = 1055.3 (4) Å30.28 × 0.05 × 0.05 mm
Data collection top
Siemens SMART CCD area-detector
diffractometer
3693 independent reflections
Radiation source: fine-focus sealed tube2097 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
Detector resolution: 8.33 pixels mm-1θmax = 25.0°, θmin = 1.8°
ω scansh = 55
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
k = 1515
Tmin = 0.995, Tmax = 0.996l = 2121
9919 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.219H-atom parameters constrained
S = 1.07 w = 1/[σ2(Fo2) + (0.0885P)2 + 0.4977P]
where P = (Fo2 + 2Fc2)/3
3693 reflections(Δ/σ)max < 0.001
275 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.21 e Å3
Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.5595 (7)0.1811 (2)0.28870 (14)0.0808 (10)
H10.42580.22810.27210.121*
O20.1919 (5)0.2991 (2)0.18760 (13)0.0596 (8)
O30.6424 (6)0.1018 (2)0.02578 (15)0.0735 (9)
O40.1972 (5)0.41094 (18)0.09103 (13)0.0544 (7)
H40.10950.38980.13250.082*
O50.1842 (5)0.34737 (19)0.15961 (13)0.0561 (7)
C10.6553 (8)0.1338 (3)0.2325 (2)0.0542 (10)
C20.8819 (8)0.0511 (3)0.2500 (2)0.0592 (11)
H20.96330.03200.29930.071*
C30.9887 (8)0.0031 (3)0.1965 (2)0.0495 (9)
C40.8717 (7)0.0282 (3)0.1226 (2)0.0450 (9)
H4A0.94550.00680.08570.054*
C50.6486 (7)0.1102 (3)0.10327 (19)0.0405 (8)
C60.5319 (7)0.1649 (3)0.15817 (19)0.0432 (9)
C70.2916 (7)0.2510 (3)0.1378 (2)0.0427 (9)
C80.1669 (7)0.2788 (2)0.06126 (18)0.0385 (8)
C90.2770 (7)0.2259 (2)0.00469 (19)0.0371 (8)
C100.5303 (7)0.1413 (3)0.02410 (19)0.0418 (9)
C110.1556 (7)0.2514 (3)0.06733 (19)0.0422 (9)
H110.23110.21600.10390.051*
C120.0821 (7)0.3308 (3)0.08654 (19)0.0428 (9)
C130.1932 (7)0.3849 (3)0.0330 (2)0.0434 (9)
H130.34800.43880.04620.052*
C140.0732 (7)0.3585 (2)0.04039 (19)0.0388 (8)
C150.4333 (8)0.4258 (3)0.1864 (2)0.0544 (10)
H15A0.37380.49600.19430.065*
H15B0.58110.42250.15010.065*
C160.5495 (8)0.4014 (3)0.2577 (2)0.0548 (10)
H160.62830.33790.25400.066*
C170.5570 (9)0.4573 (3)0.3259 (2)0.0630 (11)
C180.6733 (11)0.4216 (4)0.3946 (2)0.0799 (14)
H18A0.51730.41880.42840.096*
H18B0.82780.47530.41960.096*
C190.7924 (11)0.3171 (4)0.3844 (2)0.0851 (15)
H19A0.64440.26290.35680.102*
H19B0.96070.32070.35450.102*
C200.8810 (12)0.2864 (4)0.4569 (3)0.0998 (18)
H201.01080.33640.48930.120*
C210.8032 (10)0.1998 (4)0.4814 (2)0.0741 (13)
C220.5917 (16)0.1116 (4)0.4367 (3)0.127 (2)
H22A0.50660.13480.39390.191*
H22B0.43980.09160.46770.191*
H22C0.69320.05210.42000.191*
C230.9084 (14)0.1792 (5)0.5568 (3)0.116 (2)
H23A1.04040.23890.58250.174*
H23B1.00830.11760.55000.174*
H23C0.74400.16820.58620.174*
C241.2268 (9)0.0953 (3)0.2176 (2)0.0654 (12)
H24A1.35210.08410.25870.098*
H24B1.33990.10150.17510.098*
H24C1.14010.15900.23230.098*
C250.4357 (15)0.5620 (4)0.3414 (3)0.114 (2)
H25A0.27810.56220.30460.171*
H25B0.58770.61810.33870.171*
H25C0.36430.57220.39070.171*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.097 (2)0.098 (2)0.0436 (17)0.0224 (18)0.0083 (15)0.0274 (16)
O20.0689 (17)0.0657 (18)0.0465 (16)0.0068 (14)0.0046 (13)0.0258 (14)
O30.078 (2)0.076 (2)0.0629 (19)0.0107 (16)0.0085 (15)0.0145 (16)
O40.0631 (16)0.0506 (15)0.0509 (16)0.0098 (12)0.0073 (12)0.0229 (12)
O50.0621 (16)0.0582 (16)0.0421 (16)0.0142 (13)0.0028 (12)0.0089 (12)
C10.055 (2)0.066 (3)0.045 (2)0.009 (2)0.0024 (19)0.019 (2)
C20.061 (2)0.066 (3)0.047 (2)0.005 (2)0.0127 (19)0.005 (2)
C30.046 (2)0.048 (2)0.055 (3)0.0103 (17)0.0006 (18)0.0091 (19)
C40.044 (2)0.043 (2)0.049 (2)0.0057 (16)0.0061 (17)0.0092 (17)
C50.0401 (19)0.040 (2)0.043 (2)0.0117 (16)0.0056 (16)0.0071 (16)
C60.046 (2)0.047 (2)0.041 (2)0.0109 (17)0.0057 (17)0.0127 (17)
C70.048 (2)0.041 (2)0.044 (2)0.0098 (16)0.0112 (17)0.0162 (17)
C80.0393 (19)0.0357 (19)0.044 (2)0.0102 (15)0.0094 (16)0.0113 (16)
C90.0380 (18)0.0340 (19)0.042 (2)0.0090 (15)0.0078 (15)0.0106 (15)
C100.045 (2)0.043 (2)0.043 (2)0.0032 (16)0.0166 (17)0.0177 (17)
C110.045 (2)0.041 (2)0.042 (2)0.0040 (16)0.0072 (17)0.0119 (16)
C120.044 (2)0.043 (2)0.042 (2)0.0064 (16)0.0049 (17)0.0071 (17)
C130.042 (2)0.0345 (19)0.054 (2)0.0007 (15)0.0055 (17)0.0110 (17)
C140.0418 (19)0.0329 (19)0.046 (2)0.0067 (15)0.0090 (16)0.0144 (16)
C150.060 (2)0.046 (2)0.053 (2)0.0041 (18)0.0031 (19)0.0080 (18)
C160.067 (3)0.044 (2)0.051 (3)0.0023 (18)0.0062 (19)0.0113 (19)
C170.080 (3)0.051 (3)0.050 (3)0.010 (2)0.005 (2)0.005 (2)
C180.104 (4)0.075 (3)0.051 (3)0.013 (3)0.016 (2)0.008 (2)
C190.111 (4)0.076 (3)0.063 (3)0.011 (3)0.021 (3)0.021 (3)
C200.130 (5)0.092 (4)0.067 (3)0.023 (3)0.041 (3)0.023 (3)
C210.092 (3)0.076 (3)0.057 (3)0.015 (3)0.000 (2)0.019 (2)
C220.184 (7)0.096 (4)0.100 (4)0.006 (4)0.010 (4)0.035 (4)
C230.159 (6)0.128 (5)0.070 (4)0.025 (4)0.007 (3)0.040 (3)
C240.061 (3)0.060 (3)0.069 (3)0.002 (2)0.007 (2)0.005 (2)
C250.186 (6)0.080 (4)0.072 (4)0.031 (4)0.000 (4)0.005 (3)
Geometric parameters (Å, º) top
O1—C11.346 (4)C15—C161.470 (5)
O1—H10.82C15—H15A0.97
O2—C71.260 (4)C15—H15B0.97
O3—C101.223 (4)C16—C171.314 (5)
O4—C141.346 (3)C16—H160.93
O4—H40.82C17—C181.496 (6)
O5—C121.353 (4)C17—C251.513 (6)
O5—C151.446 (4)C18—C191.504 (6)
C1—C21.390 (5)C18—H18A0.97
C1—C61.405 (5)C18—H18B0.97
C2—C31.372 (5)C19—C201.486 (6)
C2—H20.93C19—H19A0.97
C3—C41.390 (5)C19—H19B0.97
C3—C241.509 (5)C20—C211.299 (6)
C4—C51.375 (4)C20—H200.93
C4—H4A0.93C21—C221.500 (7)
C5—C61.413 (4)C21—C231.502 (6)
C5—C101.477 (5)C22—H22A0.96
C6—C71.463 (5)C22—H22B0.96
C7—C81.441 (5)C22—H22C0.96
C8—C141.413 (4)C23—H23A0.96
C8—C91.413 (4)C23—H23B0.96
C9—C111.361 (5)C23—H23C0.96
C9—C101.490 (4)C24—H24A0.96
C11—C121.399 (5)C24—H24B0.96
C11—H110.93C24—H24C0.96
C12—C131.380 (4)C25—H25A0.96
C13—C141.382 (5)C25—H25B0.96
C13—H130.93C25—H25C0.96
C1—O1—H1109.5H15A—C15—H15B108.6
C14—O4—H4109.5C17—C16—C15128.7 (4)
C12—O5—C15119.9 (3)C17—C16—H16115.6
O1—C1—C2117.8 (3)C15—C16—H16115.6
O1—C1—C6122.0 (3)C16—C17—C18123.4 (4)
C2—C1—C6120.1 (3)C16—C17—C25122.1 (4)
C3—C2—C1121.8 (3)C18—C17—C25114.4 (4)
C3—C2—H2119.1C17—C18—C19117.9 (4)
C1—C2—H2119.1C17—C18—H18A107.8
C2—C3—C4118.6 (3)C19—C18—H18A107.8
C2—C3—C24120.7 (3)C17—C18—H18B107.8
C4—C3—C24120.7 (3)C19—C18—H18B107.8
C5—C4—C3121.1 (3)H18A—C18—H18B107.2
C5—C4—H4A119.4C20—C19—C18113.0 (4)
C3—C4—H4A119.4C20—C19—H19A109.0
C4—C5—C6120.8 (3)C18—C19—H19A109.0
C4—C5—C10119.6 (3)C20—C19—H19B109.0
C6—C5—C10119.7 (3)C18—C19—H19B109.0
C1—C6—C5117.6 (3)H19A—C19—H19B107.8
C1—C6—C7121.6 (3)C21—C20—C19129.3 (5)
C5—C6—C7120.8 (3)C21—C20—H20115.3
O2—C7—C8120.5 (3)C19—C20—H20115.3
O2—C7—C6119.8 (3)C20—C21—C22122.2 (4)
C8—C7—C6119.7 (3)C20—C21—C23123.8 (5)
C14—C8—C9117.6 (3)C22—C21—C23113.9 (4)
C14—C8—C7121.2 (3)C21—C22—H22A109.5
C9—C8—C7121.2 (3)C21—C22—H22B109.5
C11—C9—C8120.9 (3)H22A—C22—H22B109.5
C11—C9—C10119.6 (3)C21—C22—H22C109.5
C8—C9—C10119.5 (3)H22A—C22—H22C109.5
O3—C10—C5121.3 (3)H22B—C22—H22C109.5
O3—C10—C9119.7 (3)C21—C23—H23A109.5
C5—C10—C9119.0 (3)C21—C23—H23B109.5
C9—C11—C12120.3 (3)H23A—C23—H23B109.5
C9—C11—H11119.9C21—C23—H23C109.5
C12—C11—H11119.9H23A—C23—H23C109.5
O5—C12—C13125.3 (3)H23B—C23—H23C109.5
O5—C12—C11114.3 (3)C3—C24—H24A109.5
C13—C12—C11120.4 (3)C3—C24—H24B109.5
C12—C13—C14119.6 (3)H24A—C24—H24B109.5
C12—C13—H13120.2C3—C24—H24C109.5
C14—C13—H13120.2H24A—C24—H24C109.5
O4—C14—C13117.2 (3)H24B—C24—H24C109.5
O4—C14—C8121.7 (3)C17—C25—H25A109.5
C13—C14—C8121.2 (3)C17—C25—H25B109.5
O5—C15—C16106.6 (3)H25A—C25—H25B109.5
O5—C15—H15A110.4C17—C25—H25C109.5
C16—C15—H15A110.4H25A—C25—H25C109.5
O5—C15—H15B110.4H25B—C25—H25C109.5
C16—C15—H15B110.4
O1—C1—C2—C3178.5 (3)C4—C5—C10—C9176.4 (3)
C6—C1—C2—C30.9 (6)C6—C5—C10—C93.8 (5)
C1—C2—C3—C42.0 (6)C11—C9—C10—O36.0 (5)
C1—C2—C3—C24177.6 (4)C8—C9—C10—O3173.6 (3)
C2—C3—C4—C51.6 (5)C11—C9—C10—C5176.5 (3)
C24—C3—C4—C5178.1 (3)C8—C9—C10—C53.9 (5)
C3—C4—C5—C60.0 (5)C8—C9—C11—C120.2 (5)
C3—C4—C5—C10179.9 (3)C10—C9—C11—C12179.9 (3)
O1—C1—C6—C5179.9 (3)C15—O5—C12—C131.4 (5)
C2—C1—C6—C50.6 (5)C15—O5—C12—C11178.7 (3)
O1—C1—C6—C70.0 (6)C9—C11—C12—O5179.2 (3)
C2—C1—C6—C7179.4 (3)C9—C11—C12—C130.9 (5)
C4—C5—C6—C11.1 (5)O5—C12—C13—C14178.4 (3)
C10—C5—C6—C1178.8 (3)C11—C12—C13—C141.7 (5)
C4—C5—C6—C7179.0 (3)C12—C13—C14—O4177.4 (3)
C10—C5—C6—C71.1 (5)C12—C13—C14—C81.7 (5)
C1—C6—C7—O20.3 (5)C9—C8—C14—O4178.1 (3)
C5—C6—C7—O2179.6 (3)C7—C8—C14—O40.7 (5)
C1—C6—C7—C8178.6 (3)C9—C8—C14—C131.0 (5)
C5—C6—C7—C81.5 (5)C7—C8—C14—C13179.8 (3)
O2—C7—C8—C141.5 (5)C12—O5—C15—C16161.6 (3)
C6—C7—C8—C14177.4 (3)O5—C15—C16—C17114.2 (4)
O2—C7—C8—C9179.8 (3)C15—C16—C17—C18177.9 (4)
C6—C7—C8—C91.4 (5)C15—C16—C17—C250.4 (7)
C14—C8—C9—C110.2 (5)C16—C17—C18—C191.1 (7)
C7—C8—C9—C11179.0 (3)C25—C17—C18—C19178.7 (4)
C14—C8—C9—C10179.9 (3)C17—C18—C19—C20175.7 (4)
C7—C8—C9—C101.3 (5)C18—C19—C20—C21126.5 (6)
C4—C5—C10—O36.2 (5)C19—C20—C21—C221.0 (10)
C6—C5—C10—O3173.7 (3)C19—C20—C21—C23179.4 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O20.821.862.583 (4)146
O4—H4···O20.821.842.563 (3)146
C4—H4A···O3i0.932.543.393 (5)153
Symmetry code: (i) x2, y, z.
 

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